Jon Lester accepted the idea that “$155 million” would essentially become part of his name and uniform. Lester embraced Chicago’s obsession with sports, choosing No. 34 as a tribute to Walter Payton, Kerry Wood and Nolan Ryan. Lester had already told this to Cubs president Theo Epstein during his recruiting trip: “They’re going to burn this city down again when we win the World Series.”

Lester didn’t exactly court the Chicago media — his body language at his locker sometimes screams get off my lawn and he can look uncomfortable when he first sits down in the Wrigley Field interview room, wearing a windowpane checked sport coat instead of the T-shirt-and-sweatpants look. But Lester always warms up and answers direct questions honestly, taking full paragraphs to express his thoughts on just about any big-picture issue surrounding the team or Major League Baseball.

Lester earned the benefit of the doubt by confronting his weaknesses, admitting that he...